


A Mismatch Made in Heaven

by capsicleonyourleft



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Modern Setting, M/M, Matchmaking
Language: English
Status: Completed
Published: 2012-12-08
Updated: 2012-12-08
Packaged: 2017-11-20 15:31:20
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,949
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/586893
Author URL: https://archiveofourown.org/users/capsicleonyourleft/pseuds/capsicleonyourleft
Summary: <blockquote class="userstuff">
              <p>Dean’s not very keen on explaining he doesn’t want to go on a date with Anna’s brother because he’s smitten—and he hates, hates, hates using the word smitten—with a dark-haired stranger whose name he doesn’t know.</p>
            </blockquote>





	A Mismatch Made in Heaven

**Author's Note:**

  * For [improbability32](https://archiveofourown.org/gifts?recipient=improbability32).



> I received some fantastic prompts to work with. Unfortunately, my muse did not want to cooperate and I couldn’t do them justice. I got the sense that you like fluffy AU, so I hope this hits the spot and you enjoy it, improbability32 . Happy holidays!

 

The clack of stilettos against the linoleum floor alerts Dean to a female presence. A quick glance at the calendar on his desk confirms that it’s the dreaded first day of the month; like clockwork, Anna’s in his office within five minutes of his arrival, a stack of papers balanced on the crook of her elbow.

“There’s someone I want you to meet,” she announces, handing him the dwindling pile of articles he has to approve for the current issue.

Jesus fucking Christ. It’s too early for this shit. Dean’s already regretting not picking up a cup of coffee on his way in. (Anna’s made it _abundantly_ clear, five minutes into her job interview, that she wouldn’t be picking up dry-cleaning or brewing coffee—it’s why she’d gotten the job in the first place, twenty-three and fresh out of college. She had little experience with administrative duties and office work, but Dean knew that her no-bullshit attitude guaranteed she’d fit right in. The other candidates had showed up in well-tailored suits and polished loafers, and Dean had been tempted to walk them out the door before they introduced themselves. Dean might be the founder and editor-in-chief of _Classic Wheels_ , but he’s still a flannel-wearing, beer-drinking Average Joe.)

“We’ve been through this,” Dean replies distractedly, already making notes on the restoration spread featuring a ‘63 Chevy Corvette. It’s a sleek, muscled beauty, though it pales in comparison to Dean’s baby, which featured in their first issue. “The answer’s still no.”

“ _Dean_ ,” Anna scolds, because sometime during the year and a half she’s been working for him, she also appointed herself his personal life-coach, or something. “He’s _perfect_ for you.”

Despite himself, Dean raises a curious eyebrow, interest peaked; it’s not often that Anna tries to set him up with men. Then again, she also thought Cassie, Lisa and goddamn _Ruby_ were all perfect for him, and Dean’s sceptical this latest candidate would pan out any better. Experience taught him it’s usually better to entertain Anna’s delusions about her matchmaking abilities. He’ll avoid setting an actual time and place for the supposed date, and if he’s lucky, she’ll forget all about it in a couple of weeks. “Who is it?”

“My brother,” she says, beaming with pride, like pimping out her brother to her _boss_ is the greatest idea she’s ever had.

“Your brother?” Dean snorts. Anna’s close with her brother—some would probably say they’re codependent, but considering Dean’s attachment to his own brother, he’s not one to talk—so he’s heard a thing or five about the guy. He has a weird ass name (come to think of it, so is Anna’s full name, so it must run in the family), is around Dean’s age, nerdy, morose and into art. Not Dean’s type in the slightest. “Yeah, no.”

“Hear me out!” Anna insists, hands on her hips. She’s always been hard-headed, but this level of self-assured stubbornness indicates she’s been spending too much time around Jo. “He just moved into town a month ago. He’s thirty-two. I think—”

“Anna,” he interrupts, sorting through the piles of paper cluttering his desk. He still has to finish his editorial piece, and they have to go into print by noon. “I’m not going on a date with your brother. Now go do some work.”

Anna crosses her arms over her chest. “Give me one good reason why not.”

Dean thinks about a tan coat and mussed dark hair.

“It’s weird,” he says lamely. It’s not a lie, either—getting involved with his assistant’s family member would be _monumentally_ stupid. More than that, he doesn’t want to jeopardise the comfortable friendship they’ve settled into. Anna, however, seems to disagree, and he can tell she’s about to tear him a new one when the phone outside of his office rings. Dean gives his best shit-eating grin. “Better get to work!”

Anna turns on her heels and marches toward her desk, but he doesn’t miss the flair of her nostrils that indicates this conversation is far from over.

~*~

Dean grabs lunch in a small, intimate restaurant downtown every weekday. It’s furnished with lacquered wood that gives it a warm, homey vibe, and there’s an honest-to-God jukebox in the corner that doesn’t play Christmas music in all hours of the day. It has an ancient, authentic feel to it—none of those sleek, modern surfaces he can’t stand. Dean’s been a customer for years, has tried everything on the menu, and knows the entire staff by name. Due to its location, it attracts a versatile clientele—everything from stuffy lawyers to boisterous construction workers, regulars and passer-bys. It makes for an interesting lunch hour.

Dean takes his usual spot by the window, immediately scanning the room for a mop of dark hair. His view is blocked when Jo appears directly in front of him.

“You know, you _could_ ask the guy out instead of acting like a love-struck teenager,” she comments cheerfully. She’s wearing that smug look on her face that means she’s enjoying watching Dean make a fool out of himself.

“I don’t know what you’re talking about,” Dean denies, and his face absolutely does _not_ fall when he realizes the guy isn’t there. For the past four weeks, he’s always been there when Dean arrives, sitting on the other side of the room, a mess of papers spread in front of him and a tan trenchcoat draped on the back of his chair. Dean would watch him ignore his food in favour of tapping away at his phone with a puzzled look, his free hand curled around a steaming cup of coffee. Aside from his good looks, there is something intriguing about the guy; he’s quirky in a way Dean can’t put a finger on but knows he would enjoy. He always goes up to thank Ellen before he leaves, and he’s heard Jo raving about his tips.

Jo rolls her eyes dramatically. “Right. So, will it be the usual today, or would you like a plate of Denial instead?”

Dean glares at her and reminds himself that Ellen would, in all likelihood, have his ass if he started shit with her daughter. “The usual. Hold the snarky remarks.”

“Coming right up!” Jo smiles sweetly. “Ash! Get Winchester his usual plate of cholesterol!” she yells in the direction of the kitchen before disappearing to deal with the other customers.

Dean sighs and is about to check his phone when the guy walks in, trenchcoat folded over his arm and a dark-haired woman at his side. She’s gorgeous to behold, standing tall and confident in a skirt suit that accentuates her curves. They share a laugh as they settle three tables down, and Dean finds himself irrationally jealous. 

When his food arrives, Dean finds that he’s not that hungry anymore. He only manages two bites before he gets Jo to pack up the rest of his meal and retreats to the safety of his office.

~*~

“So you think you’re too good for my brother or something?” Anna accuses come Monday morning. There’s an undercurrent of indignation to her statement—one Dean recognizes all too well. To be honest, he’s reacted way worse to way less where Sam’s been concerned.

Dean rubs a hand over his face and lets out a weary sigh. “Look, Anna, I told you I’m not gonna go out with your brother.”

“You did,” she concedes, seeming to abandon some of her initial anger. “But you haven’t given me a reason—and none of that ‘it’s weird’ crap, Dean.”

“He’s your brother. You’re my employee. How is that _not_ weird?” 

Anna rolls her eyes. “You’re gonna have to do better than that, Dean. I’m not letting up on this one.”

Dean narrows his eyes suspiciously. “Why are you so set on making this happen?” Anna might be stubborn, but she never acts without a motive. “From everything you’ve told me about him, we have absolutely nothing in common.”

“It’s not about your interests, Dean,” Anna says in her I-know-what-I’m-talking-about tone. “It’s about who you are. You’re both stubborn, loyal to a fault, willing to sacrifice your own happiness for the sake of others—”

“Name one thing we both like,” Dean interrupts, because he’s _not_ about to be psychoanalyzed by his assistant.

“Dean, I’m trying to say—”

“See, you can’t even name _one_ thing! Are we supposed to talk about—”

“The Impala,” she announces loudly, cutting off Dean’s thought process.

“What?”

“When I first started working here, I sent him a copy of our first issue,” Anna explains. “He looked at the pictures of the Impala and said that it was evident this car was loved and well-cared for. He called her beautiful.” 

Dean can’t hide his shock; his mouth falls open and his eyes nearly bug out of his skull. The phone down the hall rings, and Anna leaves his office with a triumphant smirk.

~*~

“Are you ever going to talk to him?” Sam asks around a mouthful of rabbit food.

“Don’t speak with your mouth full, Sammy.”

“Stop deflecting,” Sam says as he puts down his fork. “You’ve been ogling him for weeks. Don’t you think you should just talk to him?” The little shit must have talked to Jo. Her loose tongue and wild imagination have gotten him in trouble before. 

“Nothing to talk about,” Dean says as he stabs his food. He looks over to the other side of the room, where the guy in question is huddled close with the dark-haired woman. They’ve been coming together for the past week, wrapped up in their own little bubble.

Dean’s typical flirting style is forward and a tad cocky, but he knows a lost cause when he sees it. It’s always trickier with guys, because there’s less of a chance of mutual interest and more of a chance for a broken nose. Sometimes it’s easier dealing with the ‘what if’ than the finality of a rejection.

~*~

Holiday parties are not Dean’s idea of a good time; the thought of tedious, awkward conversations with strangers is not an appealing one. Still, Anna invited him, and showing up for an hour or two won’t kill him.

He finds Anna’s apartment easily enough, guided by Christmas decorations and the cheerful chatter heard in the hallway. Taking a deep breath, he knocks on the door. 

“Dean!” Anna greets with a tipsy grin, wrapping her arms around his neck and kissing his cheek. “You made it!” 

“Thanks for inviting me, Anna,” he says, handing her the bottle of champagne he picked up on his way over. “Sam’s working late, but he said he’ll swing by later.”

Anna whisks him inside the apartment, thrusting a beer in his hand and starting a round of introduction to a handful of people. Dean is relieved to note there are only about twenty-five people present, some of whom he knows. He spots Ash and Pam doing shots in the kitchen, Gabe hitting on a pair of twins on the other side of the room, and Charlie making out with her girlfriend on the couch. Seeing some familiar faces puts Dean at ease, and he’s able to try and enjoy himself.

 

Fifty minutes later, Dean is itching for the comfort of his own home. He heads to the porch in search of solitude, hoping to escape the drunken chatter for a few minutes. Some fresh air might give him the courage to face another half hour and call it a night. Sam will probably be pissed if Dean leaves before he even gets there, but he’s willing to take the chance. 

The cold December weather makes Dean shiver as soon as he steps into the porch and closes the door behind him. He’s surprised when he sees a figure leaning against the railing, staring onto the street.

“Sorry, didn’t realize anyone was—” The guy turns around as Dean starts talking, and the sight of him effectively shuts Dean up.

His boxy trenchcoat hangs off his slim frame, and his hair is even messier than usual. Dean wonders if he’s been running his fingers through it like Dean’s itching to do. “It’s you,” he says dumbly, regretting the statement as soon as it’s out of his mouth.

The guy tilts his head in confusion, and Dean resists the urge to bang his head against the wall. _Of course_ he has no clue who Dean is; just because he’s been acting like a teenager with a crush for the past month and a half doesn’t mean the guy’s noticed him. 

“Um,” he says awkwardly, “sorry. I just wanted to get some fresh air. Didn’t know anyone else was out here. I’ll get out of your hair.”

“No, please,” the guy says in a deep, gravelly voice. He gestures for Dean to join him. “It’s not as if I own exclusive rights to the porch.”

Dean cracks a smile at that, coming closer to lean against the railing. He notes the guy’s nose and cheeks are red from the wind; he must have been out in the cold for some time. “I just had to get away from the commotion for a little while, y’know? This isn’t really my scene.”

The man nods in understanding. “I can relate. I am not particularly fond of social gatherings of this nature myself.”

“Yeah?” Dean prompts, hoping to keep the conversation going. “So what—or who—are you avoiding? An ex? A drunken admirer? Gabriel?”

The reaction he gets is a barely-there yet sincere smile. The guy look right at him, his eyes startlingly blue and bright. “Nothing like that, no. Everyone seems pleasant enough. I’m afraid I’m just not particularly skilled at interacting with large crowds of people. I tend to be very... forward. I don’t quite understand why people ask questions if they’re not interested in a sincere answer.”

“Beats me,” Dean shrugs. “You know, for a couple of socially-inept dudes, we’re not doing a bad job talking to each other.”

“No, I suppose not,” Blue Eyes agrees, that same tiny smile gracing his features. “I must admit, I’ve wanted to talk to you for quite some time. I almost did, a few times.”

Dean just stares, his mouth open but unable to form any words. 

“I’m sorry,” Blue Eyes says, looking embarrassed in the face of Dean’s silence. “I’ve made you uncomfortable. I didn’t mean—”

“No!” Dean protests. “You... I wish you had. Talked to me, I mean. Hell, I wish I’d talked to you. I just—I thought... aren’t you with someone?”

Another head tilt. “What do you mean?”

“That woman you’ve been coming in with for the past couple weeks? Aren’t you a...thing?”

Blue Eyes furrows his brow. “Sarah? She’s the owner of the gallery I work for. She’s my boss.

“Oh,” Dean says, feeling stupid and presumptuous and hopeful. “You seemed close.”

A nod. “We met in graduate school and recently reconnected. We’ve grown to be good friends.”

Dean has to laugh at that. It figures he’d misinterpret a situation to fit his pessimism. “Well that’s good to know.”

The man’s lips quirk up in a fond smile before his expression turns pensive. “I’m afraid I must confute your point about our improved social skills. We haven’t even properly introduced ourselves,” he points out with an amused curl of his lip. Dean tries not to stare too obviously. “I’m Castiel.”

Castiel. It’s a strange name, but it suits him.

“I’m Dean.”

Castiel’s eyebrows go up to his hairline. “Dean? You’re Anna’s boss?”

“She’s been talking about me, huh?” Dean says with a cocky smile. “How do you know Anna? You’re a friend?” And why the hell does Anna insist Dean meet her brother when her friend fits his type down to a T?

“I’m her brother.”

Dean stares at Castiel, half confused and half surprised. “You’re Anna’s brother?” he asks unnecessarily, barely registering it when Castiel nods. Now that he thinks about it, he recalls Anna referring to her brother as Cas, and mentioning he works at an art gallery as a curator. The pieces fit, and Dean is embarrassed for not putting everything together.

“Well this is...awkward.”

“Yes,” Castiel nods. “I assume Anna’s spoken to you about... she was rather enthusiastic about...”

“Setting us up, yeah,” Dean finishes. “Though, I have to say... my answer would have been entirely different if I’d known it’s you.”

Castiel’s eyes widen at the statement. “Are you saying...?”

“I’m saying... I really wish there was mistletoe around right about now so I could have an excuse to kiss you, Cas.”

Castiel rolls his eyes before taking a step forward, closing the gap between them. He runs his fingers across the lapels of Dean’s jacket. “Dean. I would like to kiss you. It seems you are expressing a similar desire. We hardly need a parasitic plant to act on it.”

Dean’s smile is toothy and probably ridiculous, but he doesn’t care. “You have a point there.” His hands travel to Castiel’s waist, pulling him in. He stares at the pink swell of Castiel’s lips for a long moment before leaning in for a kiss. Cas’ lips are softer than they look, firm and full against Dean’s mouth. 

“Cas?” Dean says when they separate.

“Yes, Dean?”

“I don’t know anything about art,” he confesses.

Castiel smiles, and this time it’s bigger and brighter. “I don’t know anything about cars.”

 

Anna and Sam find them making out in the coat closet like a pair of horny teenagers. Sam is absolutely mortified while Anna grins manically and exclaims, “ _I told you!_ ” Cas flushes red and Dean sets out to kiss him until he’s absolutely wrecked.

Turns out, nerdy, morose and into art? Totally Dean’s type.


End file.
